NZ299033A - Bis aminophenylphosphonate derivatives and medicaments - Google Patents
Bis aminophenylphosphonate derivatives and medicamentsInfo
- Publication number
- NZ299033A NZ299033A NZ299033A NZ29903396A NZ299033A NZ 299033 A NZ299033 A NZ 299033A NZ 299033 A NZ299033 A NZ 299033A NZ 29903396 A NZ29903396 A NZ 29903396A NZ 299033 A NZ299033 A NZ 299033A
- Authority
- NZ
- New Zealand
- Prior art keywords
- acid
- bis
- formula
- carbonylamino
- compound
- Prior art date
Links
- BMYBKYQDGKGCSU-UHFFFAOYSA-N (2-aminophenyl)phosphonic acid Chemical class NC1=CC=CC=C1P(O)(O)=O BMYBKYQDGKGCSU-UHFFFAOYSA-N 0.000 title description 3
- 239000003814 drug Substances 0.000 title 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 140
- 229910052739 hydrogen Inorganic materials 0.000 claims description 124
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 claims description 111
- 238000002360 preparation method Methods 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 89
- 239000007858 starting material Substances 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000012360 testing method Methods 0.000 claims description 8
- 238000011161 development Methods 0.000 claims description 7
- 230000012010 growth Effects 0.000 claims description 7
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 claims description 7
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims description 6
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229960005314 suramin Drugs 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 5
- 206010029113 Neovascularisation Diseases 0.000 claims description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000005690 diesters Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims description 4
- 230000003013 cytotoxicity Effects 0.000 claims description 4
- 231100000135 cytotoxicity Toxicity 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 231100000433 cytotoxic Toxicity 0.000 claims description 2
- 230000001472 cytotoxic effect Effects 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- 101100173542 Caenorhabditis elegans fer-1 gene Proteins 0.000 claims 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- UJHBVMHOBZBWMX-UHFFFAOYSA-N ferrostatin-1 Chemical compound NC1=CC(C(=O)OCC)=CC=C1NC1CCCCC1 UJHBVMHOBZBWMX-UHFFFAOYSA-N 0.000 claims 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- 230000014399 negative regulation of angiogenesis Effects 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 229940100445 wheat starch Drugs 0.000 claims 1
- 238000002844 melting Methods 0.000 description 137
- 230000008018 melting Effects 0.000 description 137
- 238000004452 microanalysis Methods 0.000 description 122
- 229910052757 nitrogen Inorganic materials 0.000 description 113
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- 239000000047 product Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 238000000034 method Methods 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- OIGQTUBEBRLSOX-UHFFFAOYSA-N 4-diethoxyphosphorylaniline Chemical compound CCOP(=O)(OCC)C1=CC=C(N)C=C1 OIGQTUBEBRLSOX-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 14
- -1 troches Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- BFDYSJCMAFSRDH-UHFFFAOYSA-N 2-phenylethylphosphonic acid Chemical compound OP(O)(=O)CCC1=CC=CC=C1 BFDYSJCMAFSRDH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 8
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 230000033115 angiogenesis Effects 0.000 description 6
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 6
- VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- PGKQTZHDCHKDQK-VOTSOKGWSA-N [(e)-2-phenylethenyl]phosphonic acid Chemical compound OP(O)(=O)\C=C\C1=CC=CC=C1 PGKQTZHDCHKDQK-VOTSOKGWSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 210000003711 chorioallantoic membrane Anatomy 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- BTZVDPWKGXMQFW-UHFFFAOYSA-N Pentadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCC(O)=O BTZVDPWKGXMQFW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OXWXINKWKITCIH-UHFFFAOYSA-N (3-nitrophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=CC([N+]([O-])=O)=C1 OXWXINKWKITCIH-UHFFFAOYSA-N 0.000 description 3
- BXZQNBQBZLWKSR-UHFFFAOYSA-N 3-[4-(2-carboxyethenyl)naphthalen-1-yl]prop-2-enoic acid Chemical compound C1=CC=C2C(C=CC(=O)O)=CC=C(C=CC(O)=O)C2=C1 BXZQNBQBZLWKSR-UHFFFAOYSA-N 0.000 description 3
- VNYWYDYKHQONQN-UHFFFAOYSA-N 4-(2-diethoxyphosphorylethenyl)aniline Chemical compound CCOP(=O)(OCC)C=CC1=CC=C(N)C=C1 VNYWYDYKHQONQN-UHFFFAOYSA-N 0.000 description 3
- RFZQQLXPUHPNTH-UHFFFAOYSA-N 4-(2-diethoxyphosphorylethyl)aniline Chemical compound CCOP(=O)(OCC)CCC1=CC=C(N)C=C1 RFZQQLXPUHPNTH-UHFFFAOYSA-N 0.000 description 3
- ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)aniline Chemical compound CCOP(=O)(OCC)CC1=CC=C(N)C=C1 ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- CNXXEPWXNDFGIG-UHFFFAOYSA-N dodecanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCCCC(Cl)=O CNXXEPWXNDFGIG-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- DDELNYCCLMDJOH-UHFFFAOYSA-N undecanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCCC(Cl)=O DDELNYCCLMDJOH-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- DAENJGZHSJAQRL-UHFFFAOYSA-N 1-(2-diethoxyphosphorylethenyl)-4-nitrobenzene Chemical compound CCOP(=O)(OCC)C=CC1=CC=C([N+]([O-])=O)C=C1 DAENJGZHSJAQRL-UHFFFAOYSA-N 0.000 description 2
- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 description 2
- XCXJLWLQQPJVDR-UHFFFAOYSA-N 3-(azepan-2-yl)quinoline Chemical compound C1CCCCNC1C1=CN=C(C=CC=C2)C2=C1 XCXJLWLQQPJVDR-UHFFFAOYSA-N 0.000 description 2
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 2
- QGJNKGPCTYCXLD-UHFFFAOYSA-N 3-[10-(2-carboxyethenyl)anthracen-9-yl]prop-2-enoic acid Chemical compound C1=CC=C2C(C=CC(=O)O)=C(C=CC=C3)C3=C(C=CC(O)=O)C2=C1 QGJNKGPCTYCXLD-UHFFFAOYSA-N 0.000 description 2
- QQOPURJHCBXZSI-UHFFFAOYSA-N 3-[5-(2-carboxyethenyl)furan-2-yl]prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(C=CC(O)=O)O1 QQOPURJHCBXZSI-UHFFFAOYSA-N 0.000 description 2
- FHZOVGZTZSYHJD-UHFFFAOYSA-N 3-[5-(2-carboxyethenyl)thiophen-2-yl]prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(C=CC(O)=O)S1 FHZOVGZTZSYHJD-UHFFFAOYSA-N 0.000 description 2
- YYZRWRZXVYMNCO-UHFFFAOYSA-N 3-[6-(2-carboxyethenyl)-9-ethylcarbazol-3-yl]prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C2N(CC)C3=CC=C(C=CC(O)=O)C=C3C2=C1 YYZRWRZXVYMNCO-UHFFFAOYSA-N 0.000 description 2
- QDBOAKPEXMMQFO-UHFFFAOYSA-N 4-(4-carbonochloridoylphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=C(C(Cl)=O)C=C1 QDBOAKPEXMMQFO-UHFFFAOYSA-N 0.000 description 2
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 description 2
- MYFXCPANJUZOOT-UHFFFAOYSA-N 9-ethylcarbazole-3,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=C2N(CC)C3=CC=C(C(O)=O)C=C3C2=C1 MYFXCPANJUZOOT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- 210000003837 chick embryo Anatomy 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000007398 colorimetric assay Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000007163 homologation reaction Methods 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SIGOIUCRXKUEIG-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylacetate Chemical compound COC(=O)CP(=O)(OC)OC SIGOIUCRXKUEIG-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- QINHATVIQFBMNQ-UHFFFAOYSA-N tridecanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCCCCC(Cl)=O QINHATVIQFBMNQ-UHFFFAOYSA-N 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- RCVWEARHYVHQBJ-UHFFFAOYSA-N 2-[3-(2-chloro-2-oxoethyl)phenyl]acetyl chloride Chemical compound ClC(=O)CC1=CC=CC(CC(Cl)=O)=C1 RCVWEARHYVHQBJ-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- VYAKDQXTHDTNJE-UHFFFAOYSA-N 2-[4-[[11-[4-(2-diethoxyphosphorylethenyl)anilino]-11-oxoundecanoyl]amino]phenyl]ethenylphosphonic acid Chemical compound C(C)OP(OCC)(=O)C=CC1=CC=C(C=C1)NC(=O)CCCCCCCCCC(=O)NC1=CC=C(C=CP(O)(O)=O)C=C1 VYAKDQXTHDTNJE-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3882—Arylalkanephosphonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
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- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9508821A FR2736914B1 (fr) | 1995-07-21 | 1995-07-21 | Nouveaux derives d'acide aminophenylphosphonique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ299033A true NZ299033A (en) | 1997-07-27 |
Family
ID=9481204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ299033A NZ299033A (en) | 1995-07-21 | 1996-07-19 | Bis aminophenylphosphonate derivatives and medicaments |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5670493A (no) |
| EP (1) | EP0754693A3 (no) |
| JP (1) | JPH0952895A (no) |
| CN (1) | CN1063182C (no) |
| AU (1) | AU703822B2 (no) |
| CA (1) | CA2180621C (no) |
| FR (1) | FR2736914B1 (no) |
| NO (1) | NO308004B1 (no) |
| NZ (1) | NZ299033A (no) |
| ZA (1) | ZA966154B (no) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2758562B1 (fr) * | 1997-01-20 | 1999-02-19 | Adir | Nouveaux derives d'acides mixtes aminobenzyliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6096730A (en) * | 1997-07-24 | 2000-08-01 | University Of Kentucky Research Foundation | Phosphonated agents and their antiangiogenic and antitumorigenic use |
| AU8918898A (en) | 1997-08-25 | 1999-03-16 | Harold Brem | Prevention of adhesions and excessive scar formation using angiogenesis inhibi tors |
| US6673843B2 (en) * | 1999-06-30 | 2004-01-06 | Emory University | Curcumin and curcuminoid inhibition of angiogenesis |
| TWI262185B (en) * | 1999-10-01 | 2006-09-21 | Eisai Co Ltd | Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives |
| EP1234575B1 (de) * | 2001-02-23 | 2004-08-18 | SIRS-Lab GmbH | Furanfettsäuren zur Steigerung der Effizienz der Zytostatikatherapie und/oder Bestrahlungstherapie |
| US20060229239A9 (en) * | 2002-03-08 | 2006-10-12 | Mamoru Shoji | Novel curcuminoid-factor VIIa constructs as suppressors of tumor growth and angiogenesis |
| ES2463490T3 (es) * | 2006-08-23 | 2014-05-28 | Novartis Ag | Amidas como inhibidores de la esfingomielina |
| US20100132796A1 (en) * | 2008-11-28 | 2010-06-03 | Samsung Electro-Mechanics Co., Ltd. | Dye compound for dye-sensitized solar cells, dye-sensitized photoelectric converter and dye-sensitized solar cells |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU547451A1 (ru) * | 1975-07-24 | 1977-02-25 | Военная Краснознаменная Академия Химической Защиты Имени Маршала Советского Союза С.К.Тимошенко | Способ получени -фенил- или -бензиламинометилфосфоновых кислот |
| DE3362581D1 (en) * | 1982-04-23 | 1986-04-24 | Ciba Geigy Ag | Herbicide and plant-growth regulator product |
| US4591582A (en) * | 1984-04-17 | 1986-05-27 | Research Corporation | Organophosphorus compounds useful as anticonvulsant agents |
| AU5640390A (en) * | 1989-06-16 | 1991-01-08 | Upjohn Company, The | Suramin type compounds and angiostatic steroids to inhibit angiogenesis |
| GB9403909D0 (en) * | 1994-03-01 | 1994-04-20 | Erba Carlo Spa | Ureido derivatives of naphthalenephosphonic acids and process for their preparation |
| US5734081A (en) * | 1994-08-05 | 1998-03-31 | Warner-Lambert Company | Arylthio compounds |
-
1995
- 1995-07-21 FR FR9508821A patent/FR2736914B1/fr not_active Expired - Fee Related
-
1996
- 1996-07-05 CA CA002180621A patent/CA2180621C/fr not_active Expired - Fee Related
- 1996-07-17 JP JP8187255A patent/JPH0952895A/ja active Pending
- 1996-07-18 EP EP96401594A patent/EP0754693A3/fr not_active Withdrawn
- 1996-07-19 NO NO963024A patent/NO308004B1/no not_active IP Right Cessation
- 1996-07-19 NZ NZ299033A patent/NZ299033A/en unknown
- 1996-07-19 AU AU60584/96A patent/AU703822B2/en not_active Ceased
- 1996-07-19 CN CN96110668A patent/CN1063182C/zh not_active Expired - Fee Related
- 1996-07-19 US US08/684,469 patent/US5670493A/en not_active Expired - Fee Related
- 1996-07-19 ZA ZA966154A patent/ZA966154B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5670493A (en) | 1997-09-23 |
| AU703822B2 (en) | 1999-04-01 |
| JPH0952895A (ja) | 1997-02-25 |
| CN1063182C (zh) | 2001-03-14 |
| ZA966154B (en) | 1997-01-23 |
| CA2180621C (fr) | 2000-02-15 |
| NO963024L (no) | 1997-01-22 |
| CN1145908A (zh) | 1997-03-26 |
| FR2736914B1 (fr) | 1997-08-22 |
| CA2180621A1 (fr) | 1997-01-22 |
| EP0754693A3 (fr) | 1997-11-05 |
| NO308004B1 (no) | 2000-07-03 |
| AU6058496A (en) | 1997-01-30 |
| EP0754693A2 (fr) | 1997-01-22 |
| FR2736914A1 (fr) | 1997-01-24 |
| NO963024D0 (no) | 1996-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ASS | Change of ownership |
Owner name: LES LABORATOIRES SERVIER, FR Free format text: OLD OWNER(S): ADIR ET COMPAGNIE |